JPS6150925B2 - - Google Patents
Info
- Publication number
- JPS6150925B2 JPS6150925B2 JP54174018A JP17401879A JPS6150925B2 JP S6150925 B2 JPS6150925 B2 JP S6150925B2 JP 54174018 A JP54174018 A JP 54174018A JP 17401879 A JP17401879 A JP 17401879A JP S6150925 B2 JPS6150925 B2 JP S6150925B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- pyridine
- tetrahydro
- thieno
- compound
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 24
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical group C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 12
- 229940124597 therapeutic agent Drugs 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- -1 methylenedioxy group Chemical group 0.000 claims description 10
- 230000000903 blocking effect Effects 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 102000012740 beta Adrenergic Receptors Human genes 0.000 claims description 7
- 108010079452 beta Adrenergic Receptors Proteins 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 208000007536 Thrombosis Diseases 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 125000003367 polycyclic group Chemical group 0.000 claims description 3
- PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical group ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 150000003222 pyridines Chemical class 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229960002961 ticlopidine hydrochloride Drugs 0.000 description 20
- MTKNGOHFNXIVOS-UHFFFAOYSA-N ticlopidine hydrochloride Chemical compound [H+].[Cl-].ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 MTKNGOHFNXIVOS-UHFFFAOYSA-N 0.000 description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 241001465754 Metazoa Species 0.000 description 9
- 239000002775 capsule Substances 0.000 description 9
- IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 description 8
- GOEMGAFJFRBGGG-UHFFFAOYSA-N acebutolol Chemical compound CCCC(=O)NC1=CC=C(OCC(O)CNC(C)C)C(C(C)=O)=C1 GOEMGAFJFRBGGG-UHFFFAOYSA-N 0.000 description 7
- 229960002122 acebutolol Drugs 0.000 description 7
- 229960003712 propranolol Drugs 0.000 description 7
- METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 description 6
- 229960002274 atenolol Drugs 0.000 description 6
- 229960002237 metoprolol Drugs 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 6
- 239000000454 talc Substances 0.000 description 6
- 229910052623 talc Inorganic materials 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 5
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 4
- 229930182837 (R)-adrenaline Natural products 0.000 description 4
- 235000021355 Stearic acid Nutrition 0.000 description 4
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229960005139 epinephrine Drugs 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
- 239000008117 stearic acid Substances 0.000 description 4
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- 206010028851 Necrosis Diseases 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 230000002785 anti-thrombosis Effects 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 238000010253 intravenous injection Methods 0.000 description 3
- 229960004592 isopropanol Drugs 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 229940127218 antiplatelet drug Drugs 0.000 description 2
- 239000002876 beta blocker Substances 0.000 description 2
- 229940097320 beta blocking agent Drugs 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- HQIRNZOQPUAHHV-UHFFFAOYSA-N bupranolol Chemical compound CC1=CC=C(Cl)C(OCC(O)CNC(C)(C)C)=C1 HQIRNZOQPUAHHV-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 230000000302 ischemic effect Effects 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 230000003902 lesion Effects 0.000 description 2
- 208000010125 myocardial infarction Diseases 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000017074 necrotic cell death Effects 0.000 description 2
- JZQKKSLKJUAGIC-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1C=CN2 JZQKKSLKJUAGIC-UHFFFAOYSA-N 0.000 description 2
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- IXHBTMCLRNMKHZ-UHFFFAOYSA-N (+-)-5-[3-(tert-butylamino)-2-hydroxypropoxy]-3,4-dihydronaphthalen-1(2H)-one Chemical compound O=C1CCCC2=C1C=CC=C2OCC(O)CNC(C)(C)C IXHBTMCLRNMKHZ-UHFFFAOYSA-N 0.000 description 1
- CEMAWMOMDPGJMB-CYBMUJFWSA-N (2r)-1-(propan-2-ylamino)-3-(2-prop-2-enoxyphenoxy)propan-2-ol Chemical compound CC(C)NC[C@@H](O)COC1=CC=CC=C1OCC=C CEMAWMOMDPGJMB-CYBMUJFWSA-N 0.000 description 1
- TWBNMYSKRDRHAT-RCWTXCDDSA-N (S)-timolol hemihydrate Chemical compound O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 TWBNMYSKRDRHAT-RCWTXCDDSA-N 0.000 description 1
- PJGMIUVTMMHGTP-UHFFFAOYSA-N 1-(4-nitrophenyl)-2-(propan-2-ylamino)propan-1-ol Chemical compound CC(C)NC(C)C(O)C1=CC=C([N+]([O-])=O)C=C1 PJGMIUVTMMHGTP-UHFFFAOYSA-N 0.000 description 1
- LNYSXXLKEDTQJY-UHFFFAOYSA-N 1-naphthalen-1-yl-2-(propan-2-ylamino)ethanol Chemical compound C1=CC=C2C(C(O)CNC(C)C)=CC=CC2=C1 LNYSXXLKEDTQJY-UHFFFAOYSA-N 0.000 description 1
- NXZCRZSWTPIOLN-UHFFFAOYSA-N 2-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-1-(2-methoxyphenyl)ethanol Chemical compound COC1=CC=CC=C1C(O)CN1CC(C=CS2)=C2CC1 NXZCRZSWTPIOLN-UHFFFAOYSA-N 0.000 description 1
- YAIALBLAIDSFBE-UHFFFAOYSA-N 2-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-1-(3-methoxyphenyl)ethanol Chemical compound COC1=CC=CC(C(O)CN2CC=3C=CSC=3CC2)=C1 YAIALBLAIDSFBE-UHFFFAOYSA-N 0.000 description 1
- FDZOZSUTVQRWLE-UHFFFAOYSA-N 2-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-1-phenylpropan-1-ol Chemical compound C1CC=2SC=CC=2CN1C(C)C(O)C1=CC=CC=C1 FDZOZSUTVQRWLE-UHFFFAOYSA-N 0.000 description 1
- VTLAVUOLZISLOI-UHFFFAOYSA-N 2-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-1-thiophen-2-ylethanol Chemical compound C1CC=2SC=CC=2CN1CC(O)C1=CC=CS1 VTLAVUOLZISLOI-UHFFFAOYSA-N 0.000 description 1
- KNAIIYGASYTJRS-UHFFFAOYSA-N 2-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-ylmethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CN1CC(C=CS2)=C2CC1 KNAIIYGASYTJRS-UHFFFAOYSA-N 0.000 description 1
- CTPYPCDNYYPXAG-UHFFFAOYSA-N 2-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-ylmethyl)benzonitrile Chemical compound N#CC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 CTPYPCDNYYPXAG-UHFFFAOYSA-N 0.000 description 1
- LKTHGCTVLSMQQP-UHFFFAOYSA-N 2-(tert-butylamino)-1-(2,5-dimethoxyphenyl)ethanol Chemical compound COC1=CC=C(OC)C(C(O)CNC(C)(C)C)=C1 LKTHGCTVLSMQQP-UHFFFAOYSA-N 0.000 description 1
- LRRMBZXWNPFZOM-UHFFFAOYSA-N 2-(tert-butylamino)-1-(5,6,7,8-tetrahydronaphthalen-1-yl)ethanol Chemical compound C1CCCC2=C1C=CC=C2C(O)CNC(C)(C)C LRRMBZXWNPFZOM-UHFFFAOYSA-N 0.000 description 1
- XWIPSTVKSZZCLR-UHFFFAOYSA-N 3-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-1-(4-nitrophenyl)propan-1-ol Chemical compound C1CC=2SC=CC=2CN1CCC(O)C1=CC=C([N+]([O-])=O)C=C1 XWIPSTVKSZZCLR-UHFFFAOYSA-N 0.000 description 1
- ORPYTRHNQIMZJY-UHFFFAOYSA-N 3-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-1-phenylpropan-1-ol Chemical compound C1CC=2SC=CC=2CN1CCC(O)C1=CC=CC=C1 ORPYTRHNQIMZJY-UHFFFAOYSA-N 0.000 description 1
- LWMJYQYTNYNXBP-UHFFFAOYSA-N 3-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-1-phenylpropan-1-one Chemical compound C1CC=2SC=CC=2CN1CCC(=O)C1=CC=CC=C1 LWMJYQYTNYNXBP-UHFFFAOYSA-N 0.000 description 1
- BWVDBTRXOIWAAS-UHFFFAOYSA-N 3-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-ylmethyl)phenol Chemical compound OC1=CC=CC(CN2CC=3C=CSC=3CC2)=C1 BWVDBTRXOIWAAS-UHFFFAOYSA-N 0.000 description 1
- HXRQKOOFERIYEV-UHFFFAOYSA-N 4-[2-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)-1-hydroxyethyl]phenol Chemical compound C1CC=2SC=CC=2CN1CC(O)C1=CC=C(O)C=C1 HXRQKOOFERIYEV-UHFFFAOYSA-N 0.000 description 1
- BLSIADFHTFGSDW-UHFFFAOYSA-N 4-[2-(tert-butylamino)-1-hydroxyethyl]-2-hydroxybenzamide Chemical compound CC(C)(C)NCC(O)C1=CC=C(C(N)=O)C(O)=C1 BLSIADFHTFGSDW-UHFFFAOYSA-N 0.000 description 1
- RHGBYUYSXHYOEQ-UHFFFAOYSA-N 5-(1-phenylethyl)-6,7-dihydro-4h-thieno[3,2-c]pyridine Chemical compound C1CC=2SC=CC=2CN1C(C)C1=CC=CC=C1 RHGBYUYSXHYOEQ-UHFFFAOYSA-N 0.000 description 1
- KQRQNOXFZRQYDD-UHFFFAOYSA-N 5-[(2,3,4-trimethoxyphenyl)methyl]-6,7-dihydro-4h-thieno[3,2-c]pyridine Chemical compound COC1=C(OC)C(OC)=CC=C1CN1CC(C=CS2)=C2CC1 KQRQNOXFZRQYDD-UHFFFAOYSA-N 0.000 description 1
- OUPIUMBZVFSTTM-UHFFFAOYSA-N 5-[(2-bromophenyl)methyl]-6,7-dihydro-4h-thieno[3,2-c]pyridine Chemical compound BrC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 OUPIUMBZVFSTTM-UHFFFAOYSA-N 0.000 description 1
- BOLPTHYAGIONKD-UHFFFAOYSA-N 5-[(2-fluorophenyl)methyl]-6,7-dihydro-4h-thieno[3,2-c]pyridine Chemical compound FC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 BOLPTHYAGIONKD-UHFFFAOYSA-N 0.000 description 1
- ODKMQZRUVWIXRH-UHFFFAOYSA-N 5-[(2-methoxyphenyl)methyl]-6,7-dihydro-4h-thieno[3,2-c]pyridine Chemical compound COC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 ODKMQZRUVWIXRH-UHFFFAOYSA-N 0.000 description 1
- WWCDFGZRMWMINX-UHFFFAOYSA-N 5-[(3,4,5-trimethoxyphenyl)methyl]-6,7-dihydro-4h-thieno[3,2-c]pyridine Chemical compound COC1=C(OC)C(OC)=CC(CN2CC=3C=CSC=3CC2)=C1 WWCDFGZRMWMINX-UHFFFAOYSA-N 0.000 description 1
- APRNTZNTWGGMST-UHFFFAOYSA-N 5-[(3-methoxyphenyl)methyl]-6,7-dihydro-4h-thieno[3,2-c]pyridine Chemical compound COC1=CC=CC(CN2CC=3C=CSC=3CC2)=C1 APRNTZNTWGGMST-UHFFFAOYSA-N 0.000 description 1
- CQSORHXZYHKWTG-UHFFFAOYSA-N 5-[(3-methylphenyl)methyl]-6,7-dihydro-4h-furo[3,2-c]pyridine Chemical compound CC1=CC=CC(CN2CC=3C=COC=3CC2)=C1 CQSORHXZYHKWTG-UHFFFAOYSA-N 0.000 description 1
- QZVLQUBGLKOJIR-UHFFFAOYSA-N 5-[(4-fluorophenyl)methyl]-6,7-dihydro-4h-thieno[3,2-c]pyridine Chemical compound C1=CC(F)=CC=C1CN1CC(C=CS2)=C2CC1 QZVLQUBGLKOJIR-UHFFFAOYSA-N 0.000 description 1
- PPRGPAINZGDKSG-UHFFFAOYSA-N 5-[(4-methylphenyl)methyl]-6,7-dihydro-4h-furo[3,2-c]pyridine Chemical compound C1=CC(C)=CC=C1CN1CC(C=CO2)=C2CC1 PPRGPAINZGDKSG-UHFFFAOYSA-N 0.000 description 1
- LPBHLADHFNDDTN-UHFFFAOYSA-N 5-[(4-methylphenyl)methyl]-6,7-dihydro-4h-thieno[3,2-c]pyridine Chemical compound C1=CC(C)=CC=C1CN1CC(C=CS2)=C2CC1 LPBHLADHFNDDTN-UHFFFAOYSA-N 0.000 description 1
- DBSHCYDRBLCPGO-UHFFFAOYSA-N 5-[(4-nitrophenyl)methyl]-6,7-dihydro-4h-thieno[3,2-c]pyridine Chemical compound C1=CC([N+](=O)[O-])=CC=C1CN1CC(C=CS2)=C2CC1 DBSHCYDRBLCPGO-UHFFFAOYSA-N 0.000 description 1
- PBHJQQVQTJCJCN-UHFFFAOYSA-N 5-[(5-chlorothiophen-2-yl)methyl]-6,7-dihydro-4h-thieno[3,2-c]pyridine Chemical compound S1C(Cl)=CC=C1CN1CC(C=CS2)=C2CC1 PBHJQQVQTJCJCN-UHFFFAOYSA-N 0.000 description 1
- PQPLBCRRWGSMBV-UHFFFAOYSA-N 5-[1-(2-chlorophenyl)propan-2-yl]-6,7-dihydro-4h-thieno[3,2-c]pyridine Chemical compound C1CC=2SC=CC=2CN1C(C)CC1=CC=CC=C1Cl PQPLBCRRWGSMBV-UHFFFAOYSA-N 0.000 description 1
- ZRGLFLKLPSRNEB-UHFFFAOYSA-N 5-[1-(2-chlorophenyl)propyl]-6,7-dihydro-4h-thieno[3,2-c]pyridine Chemical compound C1CC=2SC=CC=2CN1C(CC)C1=CC=CC=C1Cl ZRGLFLKLPSRNEB-UHFFFAOYSA-N 0.000 description 1
- PQZUUBDQYQEDIJ-UHFFFAOYSA-N 5-benzhydryl-6,7-dihydro-4h-thieno[3,2-c]pyridine Chemical compound C1CC=2SC=CC=2CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 PQZUUBDQYQEDIJ-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000005528 B01AC05 - Ticlopidine Substances 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 101000783577 Dendroaspis angusticeps Thrombostatin Proteins 0.000 description 1
- 101000783578 Dendroaspis jamesoni kaimosae Dendroaspin Proteins 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 208000005189 Embolism Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 208000001435 Thromboembolism Diseases 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 229960002213 alprenolol Drugs 0.000 description 1
- PAZJSJFMUHDSTF-UHFFFAOYSA-N alprenolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1CC=C PAZJSJFMUHDSTF-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 229960000330 bupranolol Drugs 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229940099112 cornstarch Drugs 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- VKMGSWIFEHZQRS-UHFFFAOYSA-N dichloroisoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(Cl)C(Cl)=C1 VKMGSWIFEHZQRS-UHFFFAOYSA-N 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000021552 granulated sugar Nutrition 0.000 description 1
- 238000010562 histological examination Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 229960002508 pindolol Drugs 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- MKYRMMMSZSVIGD-UHFFFAOYSA-N thieno[3,2-c]pyridine Chemical compound N1=CC=C2SC=CC2=C1 MKYRMMMSZSVIGD-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229960005001 ticlopidine Drugs 0.000 description 1
- 229960004605 timolol Drugs 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 239000000273 veterinary drug Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7850360A GB2038178B (en) | 1978-12-29 | 1978-12-29 | Antithrombotic therapeutic compsition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5592318A JPS5592318A (en) | 1980-07-12 |
| JPS6150925B2 true JPS6150925B2 (ru) | 1986-11-06 |
Family
ID=10502011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP17401879A Granted JPS5592318A (en) | 1978-12-29 | 1979-12-29 | Thrombosis remedy |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5592318A (ru) |
| BE (1) | BE880885A (ru) |
| DE (1) | DE2951669C2 (ru) |
| FR (1) | FR2445142A1 (ru) |
| GB (1) | GB2038178B (ru) |
| IE (1) | IE48883B1 (ru) |
| IL (1) | IL58816A (ru) |
| IT (1) | IT1162497B (ru) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI101150B (fi) * | 1991-09-09 | 1998-04-30 | Sankyo Co | Menetelmä lääkeaineina käyttökelpoisten tetrahydrotienopyridiinin johd annaisten valmistamiseksi |
| US6248729B1 (en) * | 1998-06-17 | 2001-06-19 | Bristol-Myers Squibb Co. | Combination of an ADP-receptor blocking antiplatelet drug and antihypertensive drug and a method for preventing a cerebral infarction employing such combination |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2215948B1 (ru) * | 1973-02-01 | 1976-05-14 | Centre Etd Ind Pharma | |
| FR2307538A1 (fr) * | 1975-04-18 | 1976-11-12 | Centre Etd Ind Pharma | Nouveau medicament anti-agregant plaquettaire |
-
1978
- 1978-12-29 GB GB7850360A patent/GB2038178B/en not_active Expired
-
1979
- 1979-11-22 FR FR7928799A patent/FR2445142A1/fr active Granted
- 1979-11-27 IL IL58816A patent/IL58816A/xx unknown
- 1979-11-28 IE IE2280/79A patent/IE48883B1/en not_active IP Right Cessation
- 1979-12-21 DE DE2951669A patent/DE2951669C2/de not_active Expired
- 1979-12-27 BE BE0/198764A patent/BE880885A/fr not_active IP Right Cessation
- 1979-12-28 IT IT51222/79A patent/IT1162497B/it active
- 1979-12-29 JP JP17401879A patent/JPS5592318A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2445142A1 (fr) | 1980-07-25 |
| FR2445142B1 (ru) | 1981-09-11 |
| GB2038178B (en) | 1983-03-09 |
| IL58816A (en) | 1982-07-30 |
| IT1162497B (it) | 1987-04-01 |
| GB2038178A (en) | 1980-07-23 |
| IT7951222A0 (it) | 1979-12-28 |
| JPS5592318A (en) | 1980-07-12 |
| IE792280L (en) | 1980-06-29 |
| IL58816A0 (en) | 1980-02-29 |
| DE2951669C2 (de) | 1985-08-22 |
| BE880885A (fr) | 1980-06-27 |
| IE48883B1 (en) | 1985-06-12 |
| DE2951669A1 (de) | 1980-07-17 |
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