ZA200209769B - 2-aminothiazoline derivatives and their use as no-synthase inhibitors. - Google Patents
2-aminothiazoline derivatives and their use as no-synthase inhibitors. Download PDFInfo
- Publication number
- ZA200209769B ZA200209769B ZA200209769A ZA200209769A ZA200209769B ZA 200209769 B ZA200209769 B ZA 200209769B ZA 200209769 A ZA200209769 A ZA 200209769A ZA 200209769 A ZA200209769 A ZA 200209769A ZA 200209769 B ZA200209769 B ZA 200209769B
- Authority
- ZA
- South Africa
- Prior art keywords
- dihydro
- thiazol
- ylamine
- radical
- pct
- Prior art date
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- REGFWZVTTFGQOJ-UHFFFAOYSA-N 4,5-dihydro-1,3-thiazol-2-amine Chemical class NC1=NCCS1 REGFWZVTTFGQOJ-UHFFFAOYSA-N 0.000 title claims description 8
- 239000003112 inhibitor Substances 0.000 title description 5
- -1 alkyl radical Chemical class 0.000 claims description 101
- 150000001875 compounds Chemical class 0.000 claims description 73
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 44
- 239000000203 mixture Substances 0.000 claims description 42
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 36
- 101150110920 FRO1 gene Proteins 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 30
- 150000003254 radicals Chemical class 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 16
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000002883 imidazolyl group Chemical group 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 11
- 125000000335 thiazolyl group Chemical group 0.000 claims description 11
- 125000001544 thienyl group Chemical group 0.000 claims description 11
- 125000001425 triazolyl group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 102100029438 Nitric oxide synthase, inducible Human genes 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 101710089543 Nitric oxide synthase, inducible Proteins 0.000 claims description 9
- 229910017711 NHRa Inorganic materials 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 230000006698 induction Effects 0.000 claims description 6
- KYAYLGLYJGZGQX-UHFFFAOYSA-N n'-[3-(2-amino-4,5-dihydro-1,3-thiazol-4-yl)phenyl]ethanimidamide Chemical compound CC(=N)NC1=CC=CC(C2N=C(N)SC2)=C1 KYAYLGLYJGZGQX-UHFFFAOYSA-N 0.000 claims description 6
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- AIPDZVUSWDMUQO-UHFFFAOYSA-N 4-(2h-triazol-4-ylmethyl)-4,5-dihydro-1,3-thiazol-2-amine Chemical compound C1SC(N)=NC1CC1=CNN=N1 AIPDZVUSWDMUQO-UHFFFAOYSA-N 0.000 claims description 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- 102000008299 Nitric Oxide Synthase Human genes 0.000 claims description 5
- 108010021487 Nitric Oxide Synthase Proteins 0.000 claims description 5
- 230000009471 action Effects 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 5
- YNDUJRKJOLLELA-ZCFIWIBFSA-N (4r)-4-(thiophen-2-ylmethyl)-4,5-dihydro-1,3-thiazol-2-amine Chemical compound C1SC(N)=N[C@@H]1CC1=CC=CS1 YNDUJRKJOLLELA-ZCFIWIBFSA-N 0.000 claims description 4
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 4
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 4
- VSOOPIXAJWERAW-UHFFFAOYSA-N C(C1=CC=CC=C1)C1N=C(SC1C)N.[N+](=O)([O-])C=1C=C(CC2N=C(SC2)N)C=CC1.N1=CC(=CC=C1)CC1N=C(SC1)N Chemical compound C(C1=CC=CC=C1)C1N=C(SC1C)N.[N+](=O)([O-])C=1C=C(CC2N=C(SC2)N)C=CC1.N1=CC(=CC=C1)CC1N=C(SC1)N VSOOPIXAJWERAW-UHFFFAOYSA-N 0.000 claims description 4
- FCBZUANCODZPOA-CTUJMYERSA-N N1C(=NC=C1)C[C@H]1N=C(SC1)N.N1=C(C=NC=C1)C[C@H]1N=C(SC1)N Chemical compound N1C(=NC=C1)C[C@H]1N=C(SC1)N.N1=C(C=NC=C1)C[C@H]1N=C(SC1)N FCBZUANCODZPOA-CTUJMYERSA-N 0.000 claims description 4
- 230000002159 abnormal effect Effects 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- NENGOEQSRWHDNR-UHFFFAOYSA-N 4-(pyrazin-2-ylmethyl)-4,5-dihydro-1,3-thiazol-2-amine Chemical compound C1SC(N)=NC1CC1=CN=CC=N1 NENGOEQSRWHDNR-UHFFFAOYSA-N 0.000 claims description 3
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- BBWNKUXBUPPRRD-MRVPVSSYSA-N (4r)-4-(pyridin-4-ylmethyl)-4,5-dihydro-1,3-thiazol-2-amine Chemical compound C1SC(N)=N[C@@H]1CC1=CC=NC=C1 BBWNKUXBUPPRRD-MRVPVSSYSA-N 0.000 claims description 2
- OMZRSRHXIVCFLA-QMMMGPOBSA-N (4s)-4-[(3-nitrophenyl)methyl]-4,5-dihydro-1,3-thiazol-2-amine Chemical compound C1SC(N)=N[C@H]1CC1=CC=CC([N+]([O-])=O)=C1 OMZRSRHXIVCFLA-QMMMGPOBSA-N 0.000 claims description 2
- AUAOVOKBADDORC-USJXWOKUSA-N C(=O)(O)C=1C=C(C[C@H]2N=C(SC2)N)C=CC1.C(C1=CC=CC=C1)[C@H]1N=C(SC1)N Chemical compound C(=O)(O)C=1C=C(C[C@H]2N=C(SC2)N)C=CC1.C(C1=CC=CC=C1)[C@H]1N=C(SC1)N AUAOVOKBADDORC-USJXWOKUSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 13
- 230000002265 prevention Effects 0.000 claims 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- MBIGPYFBBDEZBC-UHFFFAOYSA-N NCCCCC1N=C(SC1)N.C(=O)(O)C=1C=C(CC2N=C(SC2)N)C=CC1.C(C1=CC=CC=C1)C1N=C(SC1)N Chemical compound NCCCCC1N=C(SC1)N.C(=O)(O)C=1C=C(CC2N=C(SC2)N)C=CC1.C(C1=CC=CC=C1)C1N=C(SC1)N MBIGPYFBBDEZBC-UHFFFAOYSA-N 0.000 claims 2
- 238000010511 deprotection reaction Methods 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- MXGYBLNPILGHET-UHFFFAOYSA-N n'-(4,5-dihydro-1,3-thiazol-2-yl)butane-1,4-diamine Chemical compound NCCCCNC1=NCCS1 MXGYBLNPILGHET-UHFFFAOYSA-N 0.000 claims 2
- ZEJTWVAYQSUTHP-SECBINFHSA-N (4r)-4-benzyl-4,5-dihydro-1,3-thiazol-2-amine Chemical compound C1SC(N)=N[C@@H]1CC1=CC=CC=C1 ZEJTWVAYQSUTHP-SECBINFHSA-N 0.000 claims 1
- ARADHJRYMBISDS-WCBMZHEXSA-N (4r,5s)-4-benzyl-5-methyl-4,5-dihydro-1,3-thiazol-2-amine Chemical compound C[C@@H]1SC(N)=N[C@@H]1CC1=CC=CC=C1 ARADHJRYMBISDS-WCBMZHEXSA-N 0.000 claims 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 1
- PZVZGDBCMQBRMA-UHFFFAOYSA-N 3-pyridin-4-ylpropan-1-ol Chemical compound OCCCC1=CC=NC=C1 PZVZGDBCMQBRMA-UHFFFAOYSA-N 0.000 claims 1
- LBJUXVGPNYTVLU-UHFFFAOYSA-N 4-(1,3-thiazol-4-ylmethyl)-4,5-dihydro-1,3-thiazol-2-amine Chemical compound C1SC(N)=NC1CC1=CSC=N1 LBJUXVGPNYTVLU-UHFFFAOYSA-N 0.000 claims 1
- YGSVLWPVFZYKJF-UHFFFAOYSA-N 4-(1,3-thiazol-5-ylmethyl)-4,5-dihydro-1,3-thiazol-2-amine Chemical compound C1SC(N)=NC1CC1=CN=CS1 YGSVLWPVFZYKJF-UHFFFAOYSA-N 0.000 claims 1
- VZQMGVRUKWEXJE-UHFFFAOYSA-N 4-(cyclohexylmethyl)-4,5-dihydro-1,3-thiazol-2-amine;5-methyl-4,5-dihydro-1,3-thiazol-2-amine Chemical compound CC1CN=C(N)S1.C1SC(N)=NC1CC1CCCCC1 VZQMGVRUKWEXJE-UHFFFAOYSA-N 0.000 claims 1
- CQYJBVZZXUKJOY-UHFFFAOYSA-N 4-(pyridin-3-ylmethyl)-4,5-dihydro-1,3-thiazol-2-amine Chemical compound C1SC(N)=NC1CC1=CC=CN=C1 CQYJBVZZXUKJOY-UHFFFAOYSA-N 0.000 claims 1
- YNDUJRKJOLLELA-UHFFFAOYSA-N 4-(thiophen-2-ylmethyl)-4,5-dihydro-1,3-thiazol-2-amine Chemical compound C1SC(N)=NC1CC1=CC=CS1 YNDUJRKJOLLELA-UHFFFAOYSA-N 0.000 claims 1
- HTJCDKPZFCYKNL-UHFFFAOYSA-N 4-[(2-amino-4,5-dihydro-1,3-thiazol-4-yl)methyl]phenol 4-(pyridin-4-ylsulfanylmethyl)-4,5-dihydro-1,3-thiazol-2-amine Chemical compound C1SC(N)=NC1CSC1=CC=NC=C1.C1SC(N)=NC1CC1=CC=C(O)C=C1 HTJCDKPZFCYKNL-UHFFFAOYSA-N 0.000 claims 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 1
- GBUKXKKZOGKPSD-UHFFFAOYSA-N 5-methyl-4-(pyridin-4-ylmethyl)-4,5-dihydro-1,3-thiazol-2-amine Chemical compound CC1SC(N)=NC1CC1=CC=NC=C1 GBUKXKKZOGKPSD-UHFFFAOYSA-N 0.000 claims 1
- CGAXUPZSFKZAFD-UHFFFAOYSA-N 5-methyl-4-(pyridin-4-ylmethyl)-4,5-dihydro-1,3-thiazol-2-amine 4-(pyridin-4-ylmethyl)-4,5-dihydro-1,3-thiazol-2-amine Chemical compound C1SC(N)=NC1CC1=CC=NC=C1.CC1SC(N)=NC1CC1=CC=NC=C1 CGAXUPZSFKZAFD-UHFFFAOYSA-N 0.000 claims 1
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- CGAXUPZSFKZAFD-XXIJYSMUSA-N C[C@@H]1[C@H](N=C(S1)N)CC1=CC=NC=C1.N1=CC=C(C=C1)C[C@H]1N=C(SC1)N Chemical compound C[C@@H]1[C@H](N=C(S1)N)CC1=CC=NC=C1.N1=CC=C(C=C1)C[C@H]1N=C(SC1)N CGAXUPZSFKZAFD-XXIJYSMUSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- A61P1/04—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/18—Nitrogen atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Emergency Medicine (AREA)
- Immunology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Biomedical Technology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0007397A FR2810037B1 (fr) | 2000-06-09 | 2000-06-09 | Utilisation de derives de 2-aminothiazoline comme inhibiteurs de no-synthase inductible |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200209769B true ZA200209769B (en) | 2004-03-02 |
Family
ID=8851134
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200209769A ZA200209769B (en) | 2000-06-09 | 2002-12-02 | 2-aminothiazoline derivatives and their use as no-synthase inhibitors. |
Country Status (29)
| Country | Link |
|---|---|
| EP (1) | EP1299365B1 (pt) |
| JP (1) | JP4238026B2 (pt) |
| KR (1) | KR20030025931A (pt) |
| CN (1) | CN1202096C (pt) |
| AP (1) | AP2002002708A0 (pt) |
| AR (1) | AR029937A1 (pt) |
| AT (1) | ATE305460T1 (pt) |
| AU (1) | AU2001266124A1 (pt) |
| BR (1) | BR0111986A (pt) |
| CA (1) | CA2411760C (pt) |
| DE (1) | DE60113689T2 (pt) |
| DK (1) | DK1299365T3 (pt) |
| DZ (1) | DZ3367A1 (pt) |
| EA (1) | EA200300010A1 (pt) |
| EC (1) | ECSP024375A (pt) |
| ES (1) | ES2248347T3 (pt) |
| FR (1) | FR2810037B1 (pt) |
| HK (1) | HK1057900A1 (pt) |
| HR (1) | HRP20020970A2 (pt) |
| HU (1) | HUP0301000A2 (pt) |
| IL (1) | IL153328A0 (pt) |
| MA (1) | MA25814A1 (pt) |
| MX (1) | MXPA02012071A (pt) |
| NO (1) | NO20025884L (pt) |
| NZ (1) | NZ522968A (pt) |
| OA (1) | OA12286A (pt) |
| PL (1) | PL360285A1 (pt) |
| WO (1) | WO2001094325A1 (pt) |
| ZA (1) | ZA200209769B (pt) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2337654T3 (es) * | 2001-09-26 | 2010-04-28 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Esfingolipidos. |
| CA2669810A1 (fr) * | 2001-11-09 | 2003-05-15 | Aventis Pharma S.A. | Composes intermediaires pour la preparation de derives de 2-amino-thiazoline |
| DE60234117D1 (de) * | 2001-11-09 | 2009-12-03 | Aventis Pharma Sa | 2-amino-4-pyridylmethyl-thiazolinderivate und ihre verwendung als induzierbare no-synthase inhibitoren |
| JP4365681B2 (ja) * | 2001-11-09 | 2009-11-18 | アベンティス・ファーマ・ソシエテ・アノニム | ２−アミノ−４−ヘテロアリールエチル−チアゾリン誘導体および誘導型ｎｏシンターゼの阻害剤としてのその使用 |
| AU2002238889A1 (en) * | 2002-03-14 | 2003-09-22 | Dainippon Pharmaceutical Co., Ltd. | Nitrogen monoxide synthase inhibitors |
| AU2003257300B2 (en) | 2002-08-07 | 2010-01-21 | Neuraxon Inc. | Amino benzothiazole compounds with NOS inhibitory activity |
| DE10332560B4 (de) * | 2003-07-11 | 2010-07-08 | Chiracon Gmbh | Verfahren zur Herstellung von ß- Heteroaryl-2-alanin-Verbindungen über 2-Amino-2-(heteroarylmethyl)-carbonsäure-Verbindungen |
| KR101800507B1 (ko) | 2015-09-18 | 2018-01-18 | 주식회사 이엔이티아이 | 자동세척 스크린과 식물정화장치를 활용하여 지속적으로 유입되는 생활하수나 공정폐수가 유입되는 오염하천정화를 위한 방법 및 그 장치 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5066662A (en) * | 1990-05-21 | 1991-11-19 | Warner-Lambert Company | Substituted oxazolidin-2-ones and 1,2,4-oxadiazolin-5-ones and derivatives thereof acting at muscarinic receptors |
| IL107771A0 (en) * | 1992-11-27 | 1994-02-27 | Wellcome Found | Pharmaceutical compositions containing isothiourea derivatives certain such novel compounds and their preparation |
| CN1077886C (zh) * | 1993-10-21 | 2002-01-16 | G·D·瑟尔公司 | 用作一氧化一氮合酶抑制剂的脒基衍生物 |
| AU4149696A (en) * | 1994-11-15 | 1996-06-06 | Merck & Co., Inc. | Substituted heterocycles as inhibitors of nitric oxide synthase |
| AU2223501A (en) * | 1999-12-24 | 2001-07-09 | Kyowa Hakko Kogyo Co. Ltd. | Fused purine derivatives |
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2000
- 2000-06-09 FR FR0007397A patent/FR2810037B1/fr not_active Expired - Fee Related
-
2001
- 2001-06-07 ES ES01943580T patent/ES2248347T3/es not_active Expired - Lifetime
- 2001-06-07 CN CNB01813386XA patent/CN1202096C/zh not_active Expired - Fee Related
- 2001-06-07 HU HU0301000A patent/HUP0301000A2/hu unknown
- 2001-06-07 DK DK01943580T patent/DK1299365T3/da active
- 2001-06-07 BR BR0111986-9A patent/BR0111986A/pt not_active Application Discontinuation
- 2001-06-07 PL PL36028501A patent/PL360285A1/xx unknown
- 2001-06-07 AR ARP010102730A patent/AR029937A1/es not_active Application Discontinuation
- 2001-06-07 CA CA002411760A patent/CA2411760C/fr not_active Expired - Fee Related
- 2001-06-07 NZ NZ522968A patent/NZ522968A/en unknown
- 2001-06-07 WO PCT/FR2001/001760 patent/WO2001094325A1/fr active IP Right Grant
- 2001-06-07 EP EP01943580A patent/EP1299365B1/fr not_active Expired - Lifetime
- 2001-06-07 AU AU2001266124A patent/AU2001266124A1/en not_active Abandoned
- 2001-06-07 DE DE60113689T patent/DE60113689T2/de not_active Expired - Lifetime
- 2001-06-07 KR KR1020027016766A patent/KR20030025931A/ko not_active Application Discontinuation
- 2001-06-07 OA OA1200200372A patent/OA12286A/fr unknown
- 2001-06-07 AT AT01943580T patent/ATE305460T1/de not_active IP Right Cessation
- 2001-06-07 JP JP2002501875A patent/JP4238026B2/ja not_active Expired - Fee Related
- 2001-06-07 IL IL15332801A patent/IL153328A0/xx unknown
- 2001-06-07 DZ DZ013367A patent/DZ3367A1/xx active
- 2001-06-07 EA EA200300010A patent/EA200300010A1/ru unknown
- 2001-06-07 AP APAP/P/2002/002708A patent/AP2002002708A0/en unknown
- 2001-06-07 MX MXPA02012071A patent/MXPA02012071A/es active IP Right Grant
-
2002
- 2002-12-02 ZA ZA200209769A patent/ZA200209769B/en unknown
- 2002-12-06 NO NO20025884A patent/NO20025884L/no not_active Application Discontinuation
- 2002-12-06 HR HR20020970A patent/HRP20020970A2/xx not_active Application Discontinuation
- 2002-12-09 EC EC2002004375A patent/ECSP024375A/es unknown
- 2002-12-09 MA MA26939A patent/MA25814A1/fr unknown
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2004
- 2004-02-06 HK HK04100771A patent/HK1057900A1/xx not_active IP Right Cessation
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