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 (sk) | 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 (sk) |
| BE (1) | BE880885A (sk) |
| DE (1) | DE2951669C2 (sk) |
| FR (1) | FR2445142A1 (sk) |
| GB (1) | GB2038178B (sk) |
| IE (1) | IE48883B1 (sk) |
| IL (1) | IL58816A (sk) |
| IT (1) | IT1162497B (sk) |
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 |
| JP4588877B2 (ja) * | 1998-06-17 | 2010-12-01 | ブリストル−マイヤーズ スクイブ カンパニー | Ａｄｐ−受容体抗血小板物質と抗高血圧薬の組合せ投与による脳梗塞の予防 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2215948B1 (sk) * | 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 |
|---|---|
| BE880885A (fr) | 1980-06-27 |
| IL58816A (en) | 1982-07-30 |
| IE48883B1 (en) | 1985-06-12 |
| IE792280L (en) | 1980-06-29 |
| IT1162497B (it) | 1987-04-01 |
| FR2445142B1 (sk) | 1981-09-11 |
| IL58816A0 (en) | 1980-02-29 |
| GB2038178B (en) | 1983-03-09 |
| DE2951669C2 (de) | 1985-08-22 |
| FR2445142A1 (fr) | 1980-07-25 |
| GB2038178A (en) | 1980-07-23 |
| IT7951222A0 (it) | 1979-12-28 |
| JPS5592318A (en) | 1980-07-12 |
| DE2951669A1 (de) | 1980-07-17 |
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