OA12286A - 2-Aminothiazoline derivatives and their use as no-synthase inhibitors. - Google Patents

2-Aminothiazoline derivatives and their use as no-synthase inhibitors. Download PDF

Info

Publication number: OA12286A
Authority: OA; OAPI
Prior art keywords: dihydro; thiazol; ylamine; temperature; radical
Prior art date: 2000-06-09

Application number

OA1200200372A

Other languages

English (en)

French (fr)

Inventor

Jean-Christophe Carry

Dominique Damour

Claude Guyon

Serge Mignani

Eric Bacque

Antony Bigot

Michel Tabart

Original Assignee

Aventis Pharma Sa

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-06-09

Filing date

2001-06-07

Publication date

2006-05-12

2001-06-07 Application filed by Aventis Pharma Sa filed Critical Aventis Pharma Sa

2006-05-12 Publication of OA12286A publication Critical patent/OA12286A/fr

Links

REGFWZVTTFGQOJ-UHFFFAOYSA-N 4,5-dihydro-1,3-thiazol-2-amine Chemical class NC1=NCCS1 REGFWZVTTFGQOJ-UHFFFAOYSA-N 0.000 title claims description 9
239000003112 inhibitor Substances 0.000 title abstract description 7
-1 pyridyl N-oxide Chemical group 0.000 claims abstract description 230
150000001875 compounds Chemical class 0.000 claims abstract description 78
150000003839 salts Chemical class 0.000 claims abstract description 38
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 32
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 29
125000004076 pyridyl group Chemical group 0.000 claims abstract description 15
125000000217 alkyl group Chemical group 0.000 claims abstract description 12
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 11
125000002883 imidazolyl group Chemical group 0.000 claims abstract description 11
125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 11
125000000335 thiazolyl group Chemical group 0.000 claims abstract description 11
125000001425 triazolyl group Chemical group 0.000 claims abstract description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 10
125000001544 thienyl group Chemical group 0.000 claims abstract description 10
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims abstract description 8
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
239000000203 mixture Substances 0.000 claims description 184
238000000034 method Methods 0.000 claims description 50
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 42
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 30
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
125000006239 protecting group Chemical group 0.000 claims description 26
230000009471 action Effects 0.000 claims description 18
150000003254 radicals Chemical group 0.000 claims description 17
150000001412 amines Chemical group 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims description 14
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 13
238000010511 deprotection reaction Methods 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 8
229910052701 rubidium Inorganic materials 0.000 claims description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
229910017711 NHRa Inorganic materials 0.000 claims description 6
230000015572 biosynthetic process Effects 0.000 claims description 6
201000010099 disease Diseases 0.000 claims description 6
230000006698 induction Effects 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
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
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 description 5
WQNMJFHOQRSBGM-UHFFFAOYSA-N 4-(pyridin-4-ylsulfanylmethyl)-4,5-dihydro-1,3-thiazol-2-amine Chemical compound C1SC(N)=NC1CSC1=CC=NC=C1 WQNMJFHOQRSBGM-UHFFFAOYSA-N 0.000 claims description 5
125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 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
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
ARADHJRYMBISDS-PSASIEDQSA-N (4r,5r)-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-PSASIEDQSA-N 0.000 claims description 4
KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [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
230000002159 abnormal effect Effects 0.000 claims description 4
OVQWHRFBVPDPCD-UHFFFAOYSA-N benzyl ethanimidothioate;hydrochloride Chemical compound Cl.CC(=N)SCC1=CC=CC=C1 OVQWHRFBVPDPCD-UHFFFAOYSA-N 0.000 claims description 4
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims description 3
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 3
125000004429 atom Chemical group 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
230000001939 inductive effect Effects 0.000 claims description 3
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 3
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 3
OMZRSRHXIVCFLA-MRVPVSSYSA-N (4r)-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-MRVPVSSYSA-N 0.000 claims description 2
LHYFIPGBGDLLRB-YFKPBYRVSA-N (4s)-4-(1h-imidazol-2-ylmethyl)-4,5-dihydro-1,3-thiazol-2-amine Chemical compound C1SC(N)=N[C@H]1CC1=NC=CN1 LHYFIPGBGDLLRB-YFKPBYRVSA-N 0.000 claims description 2
ARADHJRYMBISDS-WPRPVWTQSA-N (4s,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-WPRPVWTQSA-N 0.000 claims description 2
125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 2
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 description 2
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 2
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims 2
150000002367 halogens Chemical class 0.000 claims 2
ICOFAPJWRCLIFV-BDYWGEMQSA-N (4R,5R)-4-benzyl-5-methyl-4,5-dihydro-1,3-thiazol-2-amine (4R)-4-(thiophen-2-ylmethyl)-4,5-dihydro-1,3-thiazol-2-amine (4R)-4-(thiophen-3-ylmethyl)-4,5-dihydro-1,3-thiazol-2-amine Chemical compound S1C(=CC=C1)C[C@H]1N=C(SC1)N.S1C=C(C=C1)C[C@H]1N=C(SC1)N.C(C1=CC=CC=C1)[C@H]1N=C(S[C@@H]1C)N ICOFAPJWRCLIFV-BDYWGEMQSA-N 0.000 claims 1
CQYJBVZZXUKJOY-MRVPVSSYSA-N (4r)-4-(pyridin-3-ylmethyl)-4,5-dihydro-1,3-thiazol-2-amine Chemical compound C1SC(N)=N[C@@H]1CC1=CC=CN=C1 CQYJBVZZXUKJOY-MRVPVSSYSA-N 0.000 claims 1
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 1
BFLHUCDKEKVQHV-LURJTMIESA-N (4s)-4-(4-aminobutyl)-4,5-dihydro-1,3-thiazol-2-amine Chemical compound NCCCC[C@H]1CSC(N)=N1 BFLHUCDKEKVQHV-LURJTMIESA-N 0.000 claims 1
FVZXYJDGVYLMDB-UHFFFAOYSA-N 3-pyridin-2-ylpropan-1-ol Chemical compound OCCCC1=CC=CC=N1 FVZXYJDGVYLMDB-UHFFFAOYSA-N 0.000 claims 1
LHYFIPGBGDLLRB-UHFFFAOYSA-N 4-(1h-imidazol-2-ylmethyl)-4,5-dihydro-1,3-thiazol-2-amine Chemical compound C1SC(N)=NC1CC1=NC=CN1 LHYFIPGBGDLLRB-UHFFFAOYSA-N 0.000 claims 1
XIZWOHNOQOVEDG-UHFFFAOYSA-N 4-(1h-imidazol-2-ylmethyl)-4,5-dihydro-1,3-thiazol-2-amine;4-(1,3-thiazol-4-ylmethyl)-4,5-dihydro-1,3-thiazol-2-amine Chemical compound C1SC(N)=NC1CC1=CSC=N1.C1SC(N)=NC1CC1=NC=CN1 XIZWOHNOQOVEDG-UHFFFAOYSA-N 0.000 claims 1
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 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
CBARLASMTKMYET-UHFFFAOYSA-N 5-ethyl-4-(pyridin-4-ylmethyl)-4,5-dihydro-1,3-thiazol-2-amine Chemical compound CCC1SC(N)=NC1CC1=CC=NC=C1 CBARLASMTKMYET-UHFFFAOYSA-N 0.000 claims 1
241000283986 Lepus Species 0.000 claims 1
150000001204 N-oxides Chemical group 0.000 claims 1
QRMSKWHJHKXEPC-SYRWHEELSA-N [N+](=O)([O-])C=1C=C(C[C@@H]2N=C(SC2)N)C=CC1.NCCCC[C@H]1N=C(SC1)N.C(=O)(O)C=1C=C(C[C@H]2N=C(SC2)N)C=CC1 Chemical compound [N+](=O)([O-])C=1C=C(C[C@@H]2N=C(SC2)N)C=CC1.NCCCC[C@H]1N=C(SC1)N.C(=O)(O)C=1C=C(C[C@H]2N=C(SC2)N)C=CC1 QRMSKWHJHKXEPC-SYRWHEELSA-N 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
239000003638 chemical reducing agent Substances 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
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 1
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
ABIKNLOWSFHUPA-UHFFFAOYSA-N tert-butyl thiocyanate Chemical compound CC(C)(C)SC#N ABIKNLOWSFHUPA-UHFFFAOYSA-N 0.000 claims 1
102100029438 Nitric oxide synthase, inducible Human genes 0.000 abstract description 10
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230000002829 reductive effect Effects 0.000 description 197
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 159
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239000007787 solid Substances 0.000 description 98
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238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 59
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 56
238000006243 chemical reaction Methods 0.000 description 55
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WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
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239000000725 suspension Substances 0.000 description 34
239000000706 filtrate Substances 0.000 description 31
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235000019341 magnesium sulphate Nutrition 0.000 description 28
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238000004587 chromatography analysis Methods 0.000 description 23
238000010438 heat treatment Methods 0.000 description 23
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235000011152 sodium sulphate Nutrition 0.000 description 18
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Classifications

- 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
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- 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
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- 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
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- 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

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OA1200200372A 2000-06-09 2001-06-07 2-Aminothiazoline derivatives and their use as no-synthase inhibitors. OA12286A (en)

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
OA12286A true OA12286A (en)	2006-05-12

Family

ID=8851134

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200200372A OA12286A (en)	2000-06-09	2001-06-07	2-Aminothiazoline derivatives and their use as no-synthase inhibitors.

Country Status (28)

Country	Link
EP (1)	EP1299365B1 (de)
JP (1)	JP4238026B2 (de)
KR (1)	KR20030025931A (de)
CN (1)	CN1202096C (de)
AP (1)	AP2002002708A0 (de)
AR (1)	AR029937A1 (de)
AT (1)	ATE305460T1 (de)
AU (1)	AU2001266124A1 (de)
BR (1)	BR0111986A (de)
CA (1)	CA2411760C (de)
DE (1)	DE60113689T2 (de)
DK (1)	DK1299365T3 (de)
DZ (1)	DZ3367A1 (de)
EA (1)	EA200300010A1 (de)
EC (1)	ECSP024375A (de)
ES (1)	ES2248347T3 (de)
FR (1)	FR2810037B1 (de)
HR (1)	HRP20020970A2 (de)
HU (1)	HUP0301000A2 (de)
IL (1)	IL153328A0 (de)
MA (1)	MA25814A1 (de)
MX (1)	MXPA02012071A (de)
NO (1)	NO20025884L (de)
NZ (1)	NZ522968A (de)
OA (1)	OA12286A (de)
PL (1)	PL360285A1 (de)
WO (1)	WO2001094325A1 (de)
ZA (1)	ZA200209769B (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2005503432A (ja) *	2001-09-26	2005-02-03	イッサムリサーチディベロップメントカンパニーオブザヘブリューユニバーシティオブエルサレム	スフィンゴリピド
AU2002358874B2 (en) *	2001-11-09	2007-09-06	Aventis Pharma S.A.	2-amino-4-heteroarylethyl thiazoline derivatives and their use an inhibitors of inducible no-synthase
ES2335090T3 (es) *	2001-11-09	2010-03-22	Aventis Pharma S.A.	Derivados de 2-amino-4-piridilmetil-tiazolina y su utilizacion como inhibidores de no-sintasa reducible.
RU2004117526A (ru) *	2001-11-09	2005-04-10	Авентис Фарма С.А. (Fr)	Применение производных 2-аминотиазолина в качестве ингибиторов индуцибельной no-синтазы
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)

* Cited by examiner, † Cited by third party
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
JPH08503940A (ja) *	1992-11-27	1996-04-30	ザウエルカムファウンデーションリミテッド	酵素阻害薬
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
WO1996014842A1 (en) *	1994-11-15	1996-05-23	Merck & Co., Inc.	Substituted heterocycles as inhibitors of nitric oxide synthase
WO2001047931A1 (en) *	1999-12-24	2001-07-05	Kyowa Hakko Kogyo Co., Ltd.	Fused purine derivatives

2000
- 2000-06-09 FR FR0007397A patent/FR2810037B1/fr not_active Expired - Fee Related
2001
- 2001-06-07 DK DK01943580T patent/DK1299365T3/da active
- 2001-06-07 EP EP01943580A patent/EP1299365B1/de not_active Expired - Lifetime
- 2001-06-07 CA CA002411760A patent/CA2411760C/fr not_active Expired - Fee Related
- 2001-06-07 HR HR20020970A patent/HRP20020970A2/xx not_active Application Discontinuation
- 2001-06-07 CN CNB01813386XA patent/CN1202096C/zh not_active Expired - Fee Related
- 2001-06-07 AR ARP010102730A patent/AR029937A1/es not_active Application Discontinuation
- 2001-06-07 DE DE60113689T patent/DE60113689T2/de not_active Expired - Lifetime
- 2001-06-07 DZ DZ013367A patent/DZ3367A1/xx active
- 2001-06-07 OA OA1200200372A patent/OA12286A/fr unknown
- 2001-06-07 NZ NZ522968A patent/NZ522968A/en unknown
- 2001-06-07 HU HU0301000A patent/HUP0301000A2/hu unknown
- 2001-06-07 BR BR0111986-9A patent/BR0111986A/pt not_active Application Discontinuation
- 2001-06-07 AT AT01943580T patent/ATE305460T1/de not_active IP Right Cessation
- 2001-06-07 AU AU2001266124A patent/AU2001266124A1/en not_active Abandoned
- 2001-06-07 WO PCT/FR2001/001760 patent/WO2001094325A1/fr not_active Ceased
- 2001-06-07 EA EA200300010A patent/EA200300010A1/ru unknown
- 2001-06-07 ES ES01943580T patent/ES2248347T3/es not_active Expired - Lifetime
- 2001-06-07 MX MXPA02012071A patent/MXPA02012071A/es active IP Right Grant
- 2001-06-07 KR KR1020027016766A patent/KR20030025931A/ko not_active Withdrawn
- 2001-06-07 AP APAP/P/2002/002708A patent/AP2002002708A0/en unknown
- 2001-06-07 PL PL36028501A patent/PL360285A1/xx unknown
- 2001-06-07 JP JP2002501875A patent/JP4238026B2/ja not_active Expired - Fee Related
- 2001-06-07 IL IL15332801A patent/IL153328A0/xx unknown
2002
- 2002-12-02 ZA ZA200209769A patent/ZA200209769B/en unknown
- 2002-12-06 NO NO20025884A patent/NO20025884L/no not_active Application Discontinuation
- 2002-12-09 EC EC2002004375A patent/ECSP024375A/es unknown
- 2002-12-09 MA MA26939A patent/MA25814A1/fr unknown

Also Published As

Publication number	Publication date
HRP20020970A2 (en)	2005-02-28
EA200300010A1 (ru)	2003-06-26
NO20025884L (no)	2003-01-29
IL153328A0 (en)	2003-07-06
AR029937A1 (es)	2003-07-23
FR2810037B1 (fr)	2004-04-23
JP4238026B2 (ja)	2009-03-11
FR2810037A1 (fr)	2001-12-14
WO2001094325A1 (fr)	2001-12-13
AP2002002708A0 (en)	2002-12-31
MXPA02012071A (es)	2004-09-10
CN1202096C (zh)	2005-05-18
ZA200209769B (en)	2004-03-02
DE60113689T2 (de)	2006-07-13
ATE305460T1 (de)	2005-10-15
DK1299365T3 (da)	2006-02-06
DZ3367A1 (fr)	2001-12-13
HUP0301000A2 (hu)	2003-08-28
JP2003535853A (ja)	2003-12-02
CA2411760A1 (fr)	2001-12-13
BR0111986A (pt)	2003-04-01
MA25814A1 (fr)	2003-07-01
AU2001266124A1 (en)	2001-12-17
EP1299365B1 (de)	2005-09-28
CN1444572A (zh)	2003-09-24
KR20030025931A (ko)	2003-03-29
HK1057900A1 (en)	2004-04-23
ES2248347T3 (es)	2006-03-16
CA2411760C (fr)	2009-12-29
NO20025884D0 (no)	2002-12-06
ECSP024375A (es)	2003-02-06
DE60113689D1 (de)	2006-02-09
NZ522968A (en)	2005-07-29
PL360285A1 (en)	2004-09-06
EP1299365A1 (de)	2003-04-09

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FR2847253A1 (fr)	2004-05-21	Nouveaux derives de pyridazinones a titre de medicaments et compositions pharmaceutiques les renfermant
US20090143446A1 (en)	2009-06-04	Thiazolidinone amides, thiazolidine carboxylic acid amides, methods of making, and uses thereof
EP1446393B1 (de)	2006-03-08	2-amino-thiazolinderivate und ihre verwendung als hemmstoffe der induzierbaren no-synthase
CA2465691C (fr)	2011-07-19	Derives de 2-amino-4-heteroarylethyl thiazoline et leur utilisation comme inhibiteurs de no-synthase inductible
OA12286A (en)	2006-05-12	2-Aminothiazoline derivatives and their use as no-synthase inhibitors.
CA2465877C (fr)	2009-12-29	Utilisation de derives de 2-amino-4-pyridylmethyl-thiazoline comme inhibiteurs de non-synthase inductible
MC2264A1 (fr)	1993-04-26	Derives d'aminoacides
FR2915747A1 (fr)	2008-11-07	Derives de tri-amino-pyrimidine comme inhibiteurs de phosphatase cdc25
US6699895B2 (en)	2004-03-02	2-aminothiazoline derivatives and process for preparing the same
CA2411572C (fr)	2009-11-10	Derives de 4,5-dihydro-thiazol-2-ylamine et leur utilisation comme inhibiteurs de no synthase
FR2832152A1 (fr)	2003-05-16	Utilisation de derives de 2-amino-thiazoline comme inhibiteurs de no-synthase inductible
FR2832150A1 (fr)	2003-05-16	Utilisation de derives de 2-amino-4-pyridylmethyl-thiazoline comme inhibiteurs de no-synthase inductible
FR2832151A1 (fr)	2003-05-16	Utilisation de derives de 2-amino-4-heteroarylethyl-thiazoline comme inhibiteurs de no-synthase inductible
FR2855520A1 (fr)	2004-12-03	Nouveaux derives d'imidazoles, leur preparation et leur utilisation en tant que medicament